Vacation rentals in Monsigliolo

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Top-rated vacation rentals in Monsigliolo

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Guest favorite

A stone villa surrounded by greenery is featured under a clear blue sky. A large swimming pool reflects the sunlight, complemented by sun loungers and colorful potted flowers along the edges. The outdoor area is perfect for relaxation with scenic views of the Tuscan hills.

Villa in Castiglion Fiorentino

Tuscan charm of villa - countryside - Villa Senaia

In the charming Tuscan countryside, among olive trees and vineyards, a stone villa, in a strategic position to grasp the secrets of Tuscany and Umbria air conditioning and swimming pool with wellness area for your relaxation and comfort Villa Senaia is a large house with wooden beams, in a beautiful hillside location with idyllic views overlooking one of the favorite places in the Tuscan countryside, an attractive setting for outdoor dining, drinking Tuscan wine and listening to crickets and cicadas

4.9 out of 5 average rating, 240 reviews

Superhost

Villa in Cortona

Casa I Pini

Casa I Pini has spacious and comfortable interiors. The main building, the Leopoldina, has two entrances on the ground floor. The first access takes you directly to the spacious kitchen, equipped with everything needed for cooking and complete with dining table; the kitchens location is very convenient in order to reach the gazebo and the outdoor barbecue. On the left side of the kitchen there is a small living room with sofa, satellite TV and DVD; on the right side instead you will access ...

5.0 out of 5 average rating, 9 reviews

Top guest favorite

A charming cottage is shown with a terracotta facade and a tiled roof. A small table with two chairs is set on a patio, surrounded by potted plants. Lush greenery and trees can be seen in the background under a clear blue sky.

Guesthouse in Macciano

Tuscan cottage with an heavenly view

Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

4.97 out of 5 average rating, 251 reviews

Top guest favorite

The villa's exterior is highlighted by a modern structure with large glass doors and a gently sloping roof. It is surrounded by lush greenery and features a patio area with steps leading to the entrance. Soft lighting illuminates the garden, creating a serene evening ambiance.

Villa in Montepulciano

Amazing Tuscany Villa, FREE parking

Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking

4.92 out of 5 average rating, 337 reviews

Guest favorite

Aerial view of a scenic agriturismo surrounded by vineyards and rolling hills. The property features a pool and is framed by tall cypress trees, enhancing the natural landscape of lush green and golden fields under a partly cloudy sky.

Farm stay in Montepulciano

Rural Tuscany | Family farmstay with restaurant

Via della Stella is a charming agriturismo with a housing surface of 530m², divided over nine separate apartments. Each apartment has its own living room, kitchen and one or more bath & bedrooms. The farmhouse has a wonderful panoramic swimming pool. Its great position with view over the hills heading up to Montepulciano create a serene atmosphere. The farmhouse has been carefully decorated in rural Tuscan style. Activities such as wine tastings and cooking classes are available onsite.

4.96 out of 5 average rating, 116 reviews

Top guest favorite

An infinity pool is framed by stone decking and wooden lounge chairs, inviting relaxation. Umbrellas provide shade, while terraced gardens with olive trees rise in the background. The surrounding landscape features gently rolling hills and clear blue skies, enhancing the serene outdoor setting.

Villa in Cortona

Stunning Tuscan Villa & Panoramic Infinity Pool

Stunning Tuscan hilltop Villa, with infinity edge swimming pool, has sweeping 180° panoramic views to Cortona, Lake Trasimeno and the entire Val Di Chiana. The perfect family retreat within ancient sun-drenched olive groves. 5 Double bedrooms; 4 bathrooms; new fully integrated kitchen & dining living space; living room with fireplace; TV snug; stone BBQ & outdoor kitchen within dining terraces and gardens; covered breakfast porch; parking; private infinity pool with sunset views.

5.0 out of 5 average rating, 96 reviews

Guest favorite

Home in Cortona

[Antico Casale]Tuscan Views & Private Pool Cortona

Entire farmhouse finely restored to bring back the authentic spirit of a historic stone farmhouse in Cortona. ✔ Suitable for up to 12 guests ✔ Private swimming pool ✔ 1 km from the center of Cortona ✔ Property composed of the main farmhouse on two levels (ground floor and first floor) plus a separate dependance ✔ 3 double bedrooms, 2 twin bedrooms, 1 sofa bed ✔ 3 fully equipped kitchens, 3 full bathrooms, private parking ✔ Outdoor space with a unique view and dining tables

4.94 out of 5 average rating, 34 reviews

Top guest favorite

Home in Castiglion Fiorentino

Villa with Private Pool in the Tuscan Countryside

Modern villa with private pool, waterfall, large garden and relaxation area. Divided into: Suite with hydromassage bathtub, private bathroom and small refreshment corner; Apartment with 2 bedrooms, equipped kitchen and a second bathroom in elegant white faux marble. Perfect for families and groups up to 7. Features American BBQ, panoramic gazebo, ping pong, outdoor dining area and poolside shower. Close to Cortona, Arezzo, Montepulciano, Siena and the Crete Senesi.

5.0 out of 5 average rating, 23 reviews

Top guest favorite

A light-filled living space features a comfortable sofa and a dining table set for four. A large TV is mounted on a white cabinet, while a door leads to the bedroom area, which appears partially visible in the background. Wooden beams enhance the ceiling's charm.

Condo in Cortona

Chicca: Cortona's historic center

Bright, delightful and welcoming apartment located right in the heart of the historic center of Cortona with an unforgettable view: the town hall on one side and Lake Trasimeno and the Valdichiana on the other. The apartment has been recently renovated and consists of a living room with sofa bed, a small kitchen, a double bedroom and two bathrooms. The apartment has WiFi, heating and air conditioning, a washing machine, oven, microwave, hairdryer and flat iron.

4.98 out of 5 average rating, 224 reviews

Top guest favorite

An aerial view captures a sprawling property surrounded by greenery, featuring a refreshing pool bordered by sun loungers. Two rustic buildings are visible, along with shaded outdoor seating areas and a playground, all set against the backdrop of the Tuscan landscape.

Farm stay in Camucia

Il Giardino degli Ulivi | Casa Ippocastano

Il Giardino degli Ulivi is a farmhouse in the heart of Tuscany, surrounded by olive groves and only 3 km away from the charming town of Cortona. The property features 6 restored farmhouse apartments, each offering authentic Tuscan character, modern comforts, and private outdoor spaces. Guests can enjoy peaceful garden, scenic views, and relax by the swimming pool, as well as easy access to Tuscany’s rich history and vibrant cultural offerings.

5.0 out of 5 average rating, 26 reviews

Top guest favorite

The image captures a vibrant town square in Cortona, featuring a historic clock tower and a series of stone steps leading to a large building. Outdoor seating is visible, with visitors enjoying the sunny day, and nearby buildings display a range of architectural styles.

Home in Cortona

Casa del Passerino

Apartment located inside a historic building in Cortona, dating back to the 1500s, overlooking the city's main square... Our property, while condemning the war, dissociates itself from all racist behavior towards the Russian and Belarusian population. At Casa del Passerino, people of these nationalities are welcome and will be treated the same as everyone else. We look forward to seeing you in Tuscany!

4.94 out of 5 average rating, 225 reviews

Top guest favorite

The bedroom features a spacious double bed adorned with soft linens and cushions, complemented by subtle bedside lamps. Exposed wooden beams highlight the ceiling, while natural light filters through a window, adding warmth to the serene, neutral color palette.

Apartment in Cortona

Cortona Shabby Chic House - independent & balcony-

This is an apartment cared for by a Superhost who lives in Cortona every day. My place is located in the heart of the historic center just a few steps from the main squares and streets This cute apartment is recently renovated and sleeps up to 3 people. Independent apartment with single entrance all on one floor, with balcony. Thoughtfully furnished, equipped with all the comforts for total relaxation

4.96 out of 5 average rating, 423 reviews